144912-17-4

Basic information

• Product Name: 1H-Pyrrole, 1-methyl-2-(phenylethynyl)-
• CAS NO: 144912-17-4
• Molecular Formula: C13H11N
• Molecular Weight: 181.237
• Mol File: 144912-17-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1H-Pyrrole, 1-methyl-2-(phenylethynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrrole, 1-methyl-2-(phenylethynyl)-(144912-17-4)
• EPA Substance Registry System: 1H-Pyrrole, 1-methyl-2-(phenylethynyl)-(144912-17-4)

Safety Data

• Hazardous Substances Data: 144912-17-4(Hazardous Substances Data)

Usage

Structure

A pyrrole derivative with a methyl and a phenylethynyl substituent

Usage

Often used as a building block in the synthesis of various organic compounds and pharmaceuticals

Biological activity

Has the potential to exhibit biological activity

Relevance in fields

Of interest in medicinal chemistry and drug discovery, and may have applications in materials science and organic electronics.

Upstream product

• 536-74-3 phenylacetylene 
• 96-54-8 N-Methylpyrrole 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 591-50-4 iodobenzene 
• 67237-52-9 1-methyl-2-ethynyl-1H-pyrrole 
• 73163-64-1 2-(1-Methyl-1H-pyrrol-2-yl)-1-phenyl-2-(triphenyl-λ⁵-phosphanylidene)-ethanone 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 

Relevant articles and documents

Palladium-Catalyzed Regioselective Alkynylation of Pyrroles and Azoles under Mild Conditions: Application to the Synthesis of a Dopamine D-4 Receptor Agonist

A mild and general method for the direct alkynylation of azoles such as pyrrole, indole, and 7-azaindole is described here. Using a simple catalytic system such as Pd(OAc)2 (2.5 mol %), P(tBu)2Me·HBF4 (5 mol %), and NaOAc (2 equiv) allowed the regioselective introduction of various alkynyl residues at the C-2 position of pyrroles. Interestingly, C-2 alkynylation was also observed on C-3-substituted indoles, whereas classical C-3 alkynylation was obtained on selected unsubstituted indoles and 7-azaindole. Our methodology has been illustrated by the efficient synthesis of a potential schizophrenia drug (dopamine D-4 inhibitor).

Palladium-catalyzed oxidative cross-coupling between heterocycles and terminal alkynes with low catalyst loading

Direct: With [Pd2(dba)3] as a catalyst, the direct alkynylation of thiophenes bearing a variety of substituents has been accomplished by using terminal alkynes as alkynylating reagents. This protocol is also applicable to other electron-rich aromatic heterocycles. dba=dibenzylidenacetone. Copyright

Arylsulfonylacetylenes as alkynylating reagents of C sp 2 -H bonds activated with lithium bases

Chameleon: A new strategy for the synthesis of a wide variety of alkynyl derivatives by the reaction of substituted arylsulfonylacetylenes with organolithium species is described (see scheme). The high yields, the simplicity of the experimental procedure, the broad scope of this reaction, and the formation of Csp-C sp 2 bonds without using transition metals are the main features of this methodology. Copyright